Plasticizers are incorporated into a resin (usually a plastic or elastomer) to increase the flexibility, workability, or distensibility of the resin. The largest use of plasticizers is in the production of “plasticized” or flexible polyvinyl chloride (PVC) products. Typical uses of plasticized PVC include films, sheets, tubing, coated fabrics, wire and cable insulation and jacketing, toys, flooring materials such as vinyl sheet flooring or vinyl floor tiles, adhesives, sealants, inks, and medical products such as blood bags and tubing, and the like.
Other polymer systems that use small amounts of plasticizers include polyvinyl butyral, acrylic polymers, nylon, polyolefins, polyurethanes, and fluoroplastics. Plasticizers can also be used with rubber (although often these materials fall under the definition of extenders for rubber rather than plasticizers). A listing of the major plasticizers and their compatibilities with different polymer systems is provided in “Plasticizers,” A. D. Godwin, in Applied Polymer Science 21st Century, edited by C. D. Craver and C. E. Carraher, Elsevier (2000); pp. 157-175.
In the late 1990's and early 2000's, various compositions based on cyclohexanoate, cyclohexanedioates, and cyclohexanepolyoate esters were said to be useful for a range of goods from semi-rigid to highly flexible materials. See, for instance, WO 99/32427, WO 2004/046078, WO 2003/029339, US Patent Application No. 2006/0247461, and U.S. Pat. No. 7,297,738.
US Patent Application No. 2006/0183832 discloses a plasticizer for amorphous polyester resin which can give softness without hindering the transparency of the amorphous polyester resin, and an amorphous polyester resin composition superior in softness, transparency and heat resistance. A plasticizer for amorphous polyester resin, which is made of an ester of an (Aa) component selected from hydroxy aromatic carboxylic acid (AI), hydroxy condensed polycyclic aromatic carboxylic acid, hydroxy alicyclic carboxylic acid and others, and an (Ab) component selected from aliphatic alcohol, alicyclic alcohol, aromatic alcohol, phenol, alkylphenol, or alkylene oxide added products thereof.
Other references of interest include: U.S. Pat. Nos. 6,239,298; 6,355,186; 6,740,254; US 2011-0021680; US patent application No. 2014-0228494; U.S. Pat. No. 6,777,514; US patent application No. 2005/038283; US patent application No. 2008/0242895; U.S. Pat. Nos. 8,476,350; 2,520,084; Japanese Patent Application No. 51-070396; Japanese Patent Application No. 52-121596; Japanese Patent Application No. 60-181142; Japanese Patent Application No. 2008-H66047; U.S. Pat. No. 5,370,809; US patent application No. 2012/0108874; U.S. Pat. No. 5,138,022; “Esters of diphenic acid and their plasticizing properties”, Kulev et al., Izvestiya Tomskogo Politekhnicheskogo Instituta (1961) 111; “Synthesis of dialkyl diphenates and their properties”, Shioda et al., Yuki Gosei Kagaku Kyokaishi (1959), 17; and Clary, International Journal of Organic Chemistry, 2013, 3, 143-147.
There is increased interest in developing new plasticizers that offer good plasticizer performance characteristics (such as melting or chemical and thermal stability, pour point, glass transition, increased compatibility, good performance and/or low temperature properties) and are competitive economically. The present disclosure is directed towards plasticizers that can be made from low cost feeds and employ fewer manufacturing steps in order to meet economic and performance targets.